What you mention here is what makes me pull my hair out sometimes when I'm thinking about my handbags.
My ideal is to have "forever" bags. Ones with the quality, style and function to last for decades or even the rest of my life. So, I consciously started buying Chanel for that reason. I love and use my Chanels and feel comfortable that they have staying power in my closet (once I figured out my material preferences).
And, this makes me feel like I should buy Hermes. But, I'm just not in love with any of the styles. I have very strong like for the Kelly. But, if it weren't Hermes, I can't say I'd definitely buy it. So, I shouldn't buy it
because it's Hermes. (In contrast I'm drawn to lots of quilted flap bags. So my Chanels make sense for me to buy.)
All other brands - including to some extent
Gucci & LV - will have styles that date pretty easily. And, it's hard for me to stay in love with a bag that looks dated. Not vintage. Those are great. But, an "it" bag that has an obvious and very much past year and era - no bueno.
And many brands, like YSL or
Prada, have known quality issues. So, just why would I spend lots of money on them if I have to worry if they'll not only "date" but may not last.
Throw in that I like variety. I couldn't wear the same Kelly or Chanel flap or anything every day.
So, what to do? I'm not sure. Right now I'm buying bags I love that aren't trendy and come from quality manufacturers. And, I have to keep the size of my collection manageable so I wear all my bags. And, I try to look at resale so I can get value out if I sell a bag. And...
Sheesh! This is a lot of thinking for some sacks.

But at the end of the day, I do bristle at some of the prices - especially when the bag won't be a valued "keeper" for years to come.